EP1042426B1 - Invert emulsion drilling fluid containing mixtures of secondary esters obtained by conversion of olefins, and preparation thereof - Google Patents

Invert emulsion drilling fluid containing mixtures of secondary esters obtained by conversion of olefins, and preparation thereof Download PDF

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Publication number
EP1042426B1
EP1042426B1 EP98962028A EP98962028A EP1042426B1 EP 1042426 B1 EP1042426 B1 EP 1042426B1 EP 98962028 A EP98962028 A EP 98962028A EP 98962028 A EP98962028 A EP 98962028A EP 1042426 B1 EP1042426 B1 EP 1042426B1
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EP
European Patent Office
Prior art keywords
mixture
carboxylic acid
acid
esters
olefins
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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EP98962028A
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German (de)
English (en)
French (fr)
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EP1042426A1 (en
Inventor
Jeffery C. Gee
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Chevron Phillips Chemical Co LP
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Chevron Phillips Chemical Co LLC
Chevron Phillips Chemical Co LP
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Publication of EP1042426A1 publication Critical patent/EP1042426A1/en
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/02—Well-drilling compositions
    • C09K8/32—Non-aqueous well-drilling compositions, e.g. oil-based
    • C09K8/36—Water-in-oil emulsions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/02—Well-drilling compositions
    • C09K8/32—Non-aqueous well-drilling compositions, e.g. oil-based
    • C09K8/34—Organic liquids

Definitions

  • the invention relates to mixtures of secondary esters for use in invert drilling fluids or in water-based drilling muds, the mixtures having been produced by reaction of a carboxylic acid with olefins.
  • carboxylic acids can be added to olefins to produce secondary esters (meaning an ester in which the carbon on the alkyl chain to which the carboxylate moiety is attached is a secondary carbon, i.e. one that is covalently bound to two other carbon atoms, rather than a primary or tertiary carbon, which are covalently bound to one or three carbon atoms, respectively).
  • secondary esters meaning an ester in which the carbon on the alkyl chain to which the carboxylate moiety is attached is a secondary carbon, i.e. one that is covalently bound to two other carbon atoms, rather than a primary or tertiary carbon, which are covalently bound to one or three carbon atoms, respectively.
  • Catalysts known to be effective in such esterification reactions can be in the form of metallosilicates, especially aluminium silicates (such as zeolites or zeolite mordenites) having exchangeable cations and hydrogen ion-exchanged, layered clays.
  • metallosilicates especially aluminium silicates (such as zeolites or zeolite mordenites) having exchangeable cations and hydrogen ion-exchanged, layered clays.
  • these catalysts are often used with a strong acid added to them.
  • Stabilized pillared interlayered clay in which the pillars are formed after exchanging the natural cations of the clay with more suitable cations are known to be effective for catalyzing the esterification reaction of olefins and carboxylic acids.
  • monocarboxylic acid methylesters can be used as the continuous phase or part of the continuous phase in invert drilling muds.
  • EP-A-0386638 discloses the use of natural or synthetic esters or mixtures thereof in drilling fluids, the ester being a single secondary ester, such as isotridecyl acetate, or a mixture of esters, such as acetic esters of C 6 to C 10 alcohols.
  • EP-A-0031687 discloses the use of hydrogen ion-exchanged layered clays in organic reactions catalysed by protons, such as the reaction of olefins with carboxylic acids to produce esters
  • EP-A-0031252 discloses the use of metal cation-exchangeable layered clays in organic reactions catalysed by protons, such as again the reaction of olefins with carboxylic acids to produce esters.
  • a method for preparing an invert drilling fluid which process comprises the steps of:
  • the present invention also provides a method for preparing a water-based drilling mud which process comprises the steps of:
  • This invention relates to the use of an acid catalyst, preferably a dry (extremely low moisture) acid washed natural clay, to catalyze the addition of a C 1 -C 5 carboxylic acid to an olefin.
  • the process can utilize one acid or a mixture of acids, and it can utilize one olefin or a mixture of olefins.
  • the process can proceed in batch or continuous mode and operates at 60-300°C. In a continuous mode, the flow rate is generally 0.1-5 WHSV.
  • Some of the most surprising attributes of this invention are (1) that the catalyst must be nearly free of water in order for the esterification reaction to proceed; and (2) that olefin oligomerization is almost eliminated, as long as the concentration of carboxylic acid in the feedstock mixture is kept above about 3 wt. %.
  • these synthetic mixtures would function well as the continuous phase or part of the continuous phase of an invert mud. Because these mixtures are mixtures of esters rather than hydrocarbons, they would biodegrade more rapidly than do synthetic hydrocarbons.
  • esters currently used in the drilling industry can be produced a suitable ester mixture having a lower viscosity than esters currently in use.
  • esters derive from natural fatty acids, which are typically C 12 or heavier acids.
  • a branched C 8 or heavier alcohol which is the conventional practice used to get an ester with a sufficiently low pour point, the resulting ester is more viscous than the ones that can be achieved with the present invention.
  • F-25 (Engelhard) was dried in a vacuum oven overnight at about 200°C to remove water.
  • the dried clay granules were packed into a fixed bed, and a mixture that was 50 mole % propionic acid and 50 mole % commercial 1-tetradecene was passed over the bed at a temperature of 140°C and a flow rate of 0.5 WHSV.
  • the effluent contained about 20% secondary esters, about 10% propionic acid, about 70% C 14 olefins, and less than 1% C 14 oligomers.
  • the single most abundant ester in the mixture was 2-tetradecyl propionate, followed by 3-tetradecyl propionate, followed by 4-tetradecyl propionate, followed by 5-, 6- and 7-tetradecyl propionate.
  • the C 14 olefins in the effluent were about 70% linear internal olefins and about 30% alpha olefins.
  • the unreacted acid and olefins were separated from the esters by distillation and were suitable for recycling.
  • F-25 (Engelhard) was dried and packed into a fixed bed as in Example 1.
  • the chromatogram of Figure 2 shows the peaks for residual propionic acid and tetradecenes remaining as well as the peaks for the secondary esters formed from tetradecenes and propionic acid formed.
  • the effluent contained about 9% propionic acid, about 73% tetradecenes, and about 15% secondary esters.
  • the suitability of the C 14 propionates for use in invert drilling fluids was evaluated.
  • the invert emulsion was prepared by combining most of the components with the base fluid and mixing for 30 minutes at 48.9°C (120°F) using a Gifford Wood homogenizer. The ingredients were added in the order listed in the table below, but the last three were not added during the 30-minute homogenizer cycle. First, the slurry from the homogenizer was transferred to a dispersator, and then the barite, drilling solids, and CaCl 2 were added, and the mixture was stirred for 30 minutes.
  • Rheological properties of the resulting drilling fluid were determined at 48.9°C (120°F), before and after hot-rolling the emulsion for 16 hours at 65.6°C (150°F).
  • Component Amount C 14 Propionates 200.55 ml Water 37.1 ml Organoclay Viscosifier 3.0 g Emulsion stabilizer 8.0 g Emulsifier 4.0 g Lime 3.0 g Fluid loss additive 10.0 g
  • the drilling fluid showed the following rheological results at 48.9°C (120°F): Parameter Before hot rolling After hot rolling Fann Dial Reading @ 600rpm 81 89 Fann Dial Reading @ 300 rpm 49 54 Fann Dial Reading @ 200 rpm 37 41 Fann Dial Reading @ 100 rpm 25 28 Fann Dial Reading @ 6 rpm 11 11 Fann Dial Reading @ 3 rpm 10 10 Plastic Viscosity @ 48.9°C (120°F), cps 32 35 Yield Point, N/m 2 (lb/100 sq ft) 8.1 (17) 9.1 (19) 10 s gel strength, N/m 2 (lb/100 sq ft) 7.7 (16) 7.7 (16) 10 m gel strength N/m 2 (lb/100 sq ft) 10.5 (22) 12.9 (27) Electrical stability @ 48.9°C (120°F) 1328 1416 Oil mud alkalinity (Pom) 1.485 - Excess lime, kg/m 3 (lb/
  • the toxicity to mysid shrimp of the drilling fluid of Example 4 was evaluated according to the US EPA protocol in Appendix 3 of "Effluent Limitation Guidelines and New Source Performance Standards: Drilling Fluids Toxicity Test," Federal Register Vol. 50, No. 165, 34631-34636.
  • the drilling fluid For cuttings discharge, the drilling fluid must show an LC 50 toward mysid shrimp of at least 30,000 ppm.
  • the drilling fluid prepared using the C 14 propionates had an LC 50 of ⁇ 1,000,000 ppm, indicating the C 14 propionates make an extremely low toxicity drilling fluid.
  • the effluent contained about 20% secondary esters, about 10% propionic acid, about 70% C 12 olefins, and less than 1% C 12 oligomers.
  • the unreacted acid and olefins were separated from the esters by distillation and were suitable for recycle.
  • a mud formulated using a mixture of dodecyl propionates as the base fluid had this composition: Component Amount C 12 Propionates 200.55 ml Water 37.1 ml Organoclay Viscosifier 3.0 g Emulsion stabilizer 8.0 g Emulsifier 4.0 g Lime 3.0 g Fluid loss additive 10.0 g Rheological Modifier 0.5 g Barite 334.0 g Simulated drill solids 20.0 g CaCl 2 13.1 g
  • the drilling fluid showed the following rheological measurements at 48.9°C (120°F): Parameter Before hot rolling After hot rolling Mud density, kg/litre (lb/gal) 1.74 (14.5) - Fann Dial Reading @ 600rpm 74 70 Fann Dial Reading @ 300 rpm 45 40 Fann Dial Reading @ 200 rpm 34 30 Fann Dial Reading @ 100 rpm 21 20 Fann Dial Reading @ 6 rpm 8 8 Fann Dial Reading @ 3 rpm 7 7 Plastic Viscosity @ 48.9°C (120°F), cps 29 30 Yield Point, N/m 2 (lb/100 sq ft) 7.7 (16) 4.8 (10) 10 s gel strength, N/m 2 (lb/100 sq ft) 5.3 (11) 4.8 (10) 10 m gel strength N/m 2 (lb/100 sq ft) 6.2 (13) 6.2 (13) Electrical stability @ 48.9°C (120°F) 800 912 Oil mud alkalinity (Pom)
  • this mud showed an LC 50 of ⁇ 1,000,000 ppm SPP.
  • a mud formulated using a mixture of dodecyl propionates (50 wt. %) and tetradecyl propionates (50 wt. %) as the base fluid had this composition: Component Amount C 12 /C 14 Propionates (1:1) 200.55 ml Water 37.1 ml Organoclay Viscosifier 3.0 g Emulsion stabilizer 8.0 g Emulsifier 4.0 g Lime 3.0 g Fluid loss additive 10.0 g Rheological Modifier 0.5 g Barite 334.0 g Simulated drill solids 20.0 g CaCl 2 13.1 g
  • the drilling fluid showed the following rheological measurements at 48.9°C (120°F): Parameter Before hot rolling After hot rolling Mud density, kg/litre (lb/gal) 1.74 (14.5) - Fann Dial Reading @ 600rpm 74 79 Fann Dial Reading @ 300 rpm 45 46 Fann Dial Reading @ 200 rpm 34 34 Fann Dial Reading @ 100 rpm 21 22 Fann Dial Reading @ 6 rpm 8 8 Fann Dial Reading @ 3 rpm 7 7 Plastic viscosity @ 48.9°C (120°F), cps 32 33 Yield Point, N/m 2 (lb/100 sq ft) 6.2 (13) 6.2 (13) 10 s gel strength, N/m 2 (lb/100 sq ft) 5.7 (12) 5.3 (11) 10 m gel strength N/m 2 (lb/100 sq ft) 9.1 (19) 7.2 (15) Electrical stability @ 48.9°C (120°F) 1086 1097 Oil mud alkalinity (Po
  • this mud showed an LC 50 of ⁇ 1,000,000 ppm SPP.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Lubricants (AREA)
EP98962028A 1997-12-30 1998-12-09 Invert emulsion drilling fluid containing mixtures of secondary esters obtained by conversion of olefins, and preparation thereof Expired - Lifetime EP1042426B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/000,988 US6100223A (en) 1997-12-30 1997-12-30 Method of converting olefins into mixtures of secondary esters, products and uses thereof
US988 1997-12-30
PCT/US1998/026137 WO1999033932A1 (en) 1997-12-30 1998-12-09 Invert emulsion drilling fluid containing mixtures of secondary esters obtained by conversion of olefins, and preparation thereof

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EP1042426A1 EP1042426A1 (en) 2000-10-11
EP1042426B1 true EP1042426B1 (en) 2004-03-24

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US (2) US6100223A (zh)
EP (1) EP1042426B1 (zh)
CN (1) CN1322092C (zh)
AU (1) AU740722B2 (zh)
CA (1) CA2316245C (zh)
DE (1) DE69822663T2 (zh)
NO (1) NO20003400L (zh)
RU (1) RU2215017C2 (zh)
WO (1) WO1999033932A1 (zh)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040249229A1 (en) * 2003-06-06 2004-12-09 Gee Jeffery C. Isomerization of olefins with carboxylic acid
DE10334441A1 (de) 2003-07-29 2005-02-17 Cognis Deutschland Gmbh & Co. Kg Bohrlochbehandlungsmittel, enthaltend Ethercarbonsäuren
US20060073981A1 (en) * 2004-10-06 2006-04-06 Gee Jeffery C Methods of preparing non-aqueous fluids suitable for use in wellbore servicing fluids
EP1914288A1 (de) * 2006-10-20 2008-04-23 Cognis Oleochemicals GmbH Propylalkylester als Ölphase in Bohrlochbehandlungsmittel
US8471085B2 (en) 2008-10-31 2013-06-25 Chevron Phillips Chemical Company Lp Oligomerization catalyst system and process for oligomerizing olefins
CA2740217C (en) * 2008-10-31 2017-03-28 Chevron Phillips Chemical Company Lp System and method for deactivating and quenching an oligomerization catalyst
EP2855619B1 (en) 2012-07-26 2019-04-17 Amril AG Esters for drilling emulsions and metal working fluids
US9115556B2 (en) * 2012-11-20 2015-08-25 Chevron U.S.A. Inc. Method of using biologically-derived monoesters as drilling fluids
US9238783B2 (en) * 2012-11-20 2016-01-19 Chevron U.S.A. Inc. Monoester-based lubricants and methods of making same
US9115326B2 (en) * 2012-11-20 2015-08-25 Chevron U.S.A. Inc. Monoester-based lubricants and methods of making same
US9115303B2 (en) * 2012-11-20 2015-08-25 Chevron U.S.A. Inc. Biologically-derived monoesters as drilling fluids
CN105593334A (zh) * 2013-08-22 2016-05-18 雪佛龙美国公司 使用生物衍生的单酯作为钻井液的方法
CA2918633A1 (en) * 2013-08-22 2015-02-26 Stephen Joseph Miller Biologically-derived monoesters as drilling fluids
US9580636B2 (en) 2015-04-30 2017-02-28 Chevron Phillips Chemical Company Lp Secondary esters, methods of making, and uses thereof

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Also Published As

Publication number Publication date
US6100223A (en) 2000-08-08
NO20003400L (no) 2000-08-29
DE69822663T2 (de) 2005-02-10
WO1999033932A1 (en) 1999-07-08
US6191076B1 (en) 2001-02-20
AU1720099A (en) 1999-07-19
EP1042426A1 (en) 2000-10-11
CN1322092C (zh) 2007-06-20
CA2316245A1 (en) 1999-07-08
DE69822663D1 (de) 2004-04-29
CN1285862A (zh) 2001-02-28
AU740722B2 (en) 2001-11-15
NO20003400D0 (no) 2000-06-29
CA2316245C (en) 2009-02-10
RU2215017C2 (ru) 2003-10-27

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